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House vacation rentals in Chester

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Popular amenities for Chester house rentals

House rentals with a pool

Guest favorite
Home in Providence Forge
4.89 out of 5 average rating, 46 reviews

Beautiful country house with 5 bedrooms 4.5 baths

AbigailRating, 5 stars2 days ago
Absolutely beautiful place to stay. We enjoyed everything the home offered. Lots of things for the kids to do. My daughter enjoyed the pool very much! The home and property were better in person. Super clean and comfortable beds. I would definitely recommend and will return for sure!
Home in Creighton
4.81 out of 5 average rating, 455 reviews

Pool/Hot tub/Entire House 2100 Sq ft

EliRating, 5 stars6 days ago
Comfortable home that was exactly what my family needed. The rooms were spacious and beds comfortable. Shower on the first floor is my favorite of any place I’ve stayed. Maria was always responsible and was flexible my with requests.
Home in Blackstone
4.89 out of 5 average rating, 46 reviews

Brydie’s Suite at Meremont

BrianRating, 5 stars2 weeks ago
Highly Recommend! This place is even more beautiful in person! Super clean, cozy, and peaceful. The pool, jacuzzi, and view were amazing.we spent hours relaxing and enjoying the sunshine and omg the sunset is beautiful. The bed and couch were so comfy. our Yorkie loved running around the big yard. The area is quiet and perfect for a getaway. We enjoyed a great BBQ by the pool, and everything was just perfect,very private too. Melissa is a fantastic host,very friendly and quick to respond. Don’t hesitate to book, you’ll love it here! we drove 7 hrs+ from NYC it was worthy,definitely booking again!! Thanks for everything Melissa. Best, Brian,Kennia &Coco 🐶
Top guest favorite
Home in Carillon
5 out of 5 average rating, 25 reviews

Historic Blanton Getaway

SarahRating, 5 stars2 weeks ago
This place was great! The location makes it easy to get to many places in Richmond quickly and it was a perfect location for a family wedding in nearby Maymont. The house is beautiful and the furnishings very comfortable. The pool was a special bonus - lovely and relaxing with incredible plantings. Clearly a lot of time was spent considering what guests might want. I just wish we'd had more time to enjoy it.
Guest favorite
Home in Mechanicsville
4.78 out of 5 average rating, 9 reviews

Artfully Elegant Getaway

JoseRating, 5 stars1 month ago
Shannon’s place met our expectations. The price for our stay was more than reasonable. It’s such a quiet and calming space. Everything was super clean, and the neighbors were super friendly. Would 100% recommend it!
Guest favorite
Home in Midlothian
5 out of 5 average rating, 9 reviews

A house you wish you called home

RebeccaRating, 5 stars12 months ago
Good communication, great value, and flexible with a small adjustment that was needed. I would definitely stay there again.
Guest favorite
Home in Richmond
5 out of 5 average rating, 11 reviews

The Resort

KristenRating, 5 stars2 weeks ago
The Resort was a lovely home on a quiet street. Beautifully furnished and comfortable. Backyard was small but very well done with a pool and lots of seating. Host was friendly and responded quickly. We would definitely recommend staying here!
Home in Chesterfield
4.82 out of 5 average rating, 34 reviews

Lakefront Resort

JamesRating, 5 stars2 months ago
This house is awesome. It's huge and priced very competitively. It did have issues, but they didn't bother us too much. If you're expecting perfection from a home this size, at this location at this price, you're not being reasonable. For our needs, it was PERFECT.

Weekly house rentals

Top guest favorite
Home in Hopewell
5 out of 5 average rating, 25 reviews

City Point Cottage

AshleyRating, 5 stars1 month ago
City Point Cottage was all that we hoped it would be based on the listing and more!! The most beautiful renovations and just our style! City Point Cottage was in the perfect spot to visit my son at Ft Gregg - Adams! Caroline was an excellent host, very responsive and very clear instructions for check in/out and instructions for inside the cottage! Very cute place!
Top guest favorite
Home in Quinton
4.95 out of 5 average rating, 44 reviews

The Duck Blind located near RIC airport

GeenaRating, 5 stars2 weeks ago
Stayed at the Duck Blind for the weekend, the house was perfect for my husband and I. Very clean and had everything we needed. Would definitely stay again if in the area.
Top guest favorite
Home in Richmond
5 out of 5 average rating, 33 reviews

Brand-New Boho Family Getaway!

TrenaRating, 5 stars2 weeks ago
Perfect Haven! Loved the home. It was exactly what we needed. Lot's of space for a large family. All the amenities we needed and close to everywhere we needed to go. We truly enjoyed our stay.
Superhost
Home in Hopewell
4.79 out of 5 average rating, 29 reviews

4 Bedrooms House

AngeliqueRating, 5 stars6 days ago
Our family recently enjoyed a wonderful stay in your spacious and comfortable home. It was perfectly sized for our needs, providing ample room for everyone. We were particularly impressed by the thoughtful provision of all necessary amenities, making our stay incredibly convenient and relaxing. The peaceful location was a welcome respite, offering a tranquil atmosphere we thoroughly appreciated. The cleanliness of the property was exceptional, contributing significantly to our overall positive experience. Thank you for providing such a welcoming and well-maintained home for our family weekend. We would highly recommend your property to others.
Guest favorite
Home in Petersburgh
4.96 out of 5 average rating, 23 reviews

Fenced Yard, Swing Set: Pawfect for Family & Dogs!

JaniceRating, 5 stars1 month ago
The house was absolutely perfect and comfortable for our family! It was very clean and the beds, linens and towels were great! I will say that the one “bedroom” listed with a full bed is actually a laundry room with a bed in it off the kitchen. It turned out great for my granddaughter b/c she’s used to dark rooms but I wouldn’t necessarily list it as a bedroom for adults. Other than that, it was amazing! James was very responsive when I had some questions! Would definitely rent again if we are in the area!
Top guest favorite
Home in The Fan
5 out of 5 average rating, 38 reviews

Cupid's Hideout

IsabellaRating, 5 stars3 days ago
Alexander was a wonderful host. Very responsive and helpful. Check in was a breeze. This was located in a prime location. Tons to do within walking distance. Many excellent restaurants in the area. I highly recommend El Pope, Beauvine, Abi’s Books & Brews, and Little Mexico! The home was beautiful!!! Absolutely stunning in person. Very clean. Great amenities! It is a hidden gem! There’s tons to do if you want to drive as well. Very cute area. Well worth it!! Thank you!!
Top guest favorite
Home in Richmond
4.98 out of 5 average rating, 96 reviews

Private 2 acres. Huge yard/drive. 8 min to Airport

Victor S.Rating, 5 stars1 week ago
Great value, close to Richmond, and great communication! Home was very clean and organized!
Top guest favorite
Home in Huguenot
5 out of 5 average rating, 78 reviews

Hot Tub Oasis, Minutes from Downtown Richmond

HollyRating, 5 stars1 week ago
Clean home, safe quiet neighborhood, wonderful back yard to relax very peaceful. Had everything you can possibly need. Huge kitchen. Close to restaurants and planet fitness right down the street. Any question I had the host (Elizabeth) responded right away, very kind. We loved our stay. Thank you!

Private house rentals

Guest favorite
Home in Richmond
4.83 out of 5 average rating, 75 reviews

House full of peace, with a parking patio for 4 cars

JeanneRating, 5 stars2 weeks ago
We had a very comfortable and enjoyable stay. This older home in a quiet older neighborhood is well-maintained, thoughtfully updated, cozy, and comfortable. It was spotlessly clean, and the check-in process was a breeze. We appreciated the ample off-street parking and the layout, which easily accommodated the multiple generations of our family during our gathering in Richmond. Plus, the location was ideal—less than 15 minutes to downtown. Mayra, our host, made us feel very welcome and was quick to respond to any questions. The home was well stocked with everything we needed. (including a crib and bassinet) There is a large private fenced backyard and a nice office area. I would certainly stay here again.
Guest favorite
Home in Richmond
4.93 out of 5 average rating, 41 reviews

Spacious home near downtown RVA

AndreaRating, 5 stars1 month ago
My family needed a place within the area to stay while emergency work was being performed on our home. Booking Mateo's place was painless and easy. Mateo's place had everything we needed and was very clean, tidy, and comfortable. Mateo was a very gracious host, always friendly and responsive. I would definitely recommend Mateo's home.
Guest favorite
Home in Petersburgh
5 out of 5 average rating, 23 reviews

2-Bedroom oasis in Chesterfield

MicheleRating, 5 stars7 months ago
Ashley was amazing! When I told some issues she came and looked into it and fixed it ASAP. (Issue was very minor). The layout was great, sofas comfortable enough that you could sleep on them! Backyard was great for my two large dogs! Ashley was great! This is a perfect place for temporary housing or for like me for in between houses where I sold and had to wait a couple weeks until I could get into my new place!
Superhost
Home in Richmond
5 out of 5 average rating, 3 reviews

Elegant Retreat: Spacious with Outdoor Fireplace

AnnRating, 5 stars1 month ago
James place was very inviting. Loved sitting out on the back porch. Everything was spotless and we loved the decor. Host was very responsive and very helpful. They had a basket that had some much appreciated snacks as we got in a little late. There is a huge lovely park close by called Dorey park that you should go to. We will definitely return if we are ever in the area again.
Top guest favorite
Home in Bellevue
4.99 out of 5 average rating, 75 reviews

Charming Bungalow in the Heart of Richmond

SerenaRating, 5 stars1 day ago
Mary Kristina was a great host! Instructions were very clear and she was very helpful and responsive. The house was beautiful too!
Superhost
Home in Chesterfield
4.8 out of 5 average rating, 44 reviews

Exquisite Farmhouse Style Home

JonathanRating, 5 stars2 months ago
Close to Swim RVA and the soccer fields. much more convenient than staying on Midlothian Turnpike...and no traffic! Everyone had their own bed, and it's so nice for the adults to be able to stay up when the swimmers are early to bed early to rise. The place was clean, and we look forward to staying there again!
Guest favorite
Home in Richmond
4.95 out of 5 average rating, 38 reviews

Modern Artsy Haven with Coffee/Snack Bar/King bed

KennethRating, 5 starstoday
This place is great the decor is A1 the master bedroom is simply amazing the soaker tub was a really nice touch the access to snacks,water,coffee & juice was a added bonus adequate space for a party of 5 the upstairs has its own living room which was nice for my kids to hang out I am super impressed
Guest favorite
Home in Richmond
4.93 out of 5 average rating, 14 reviews

Entire Cozy Home in Richmond

ByrdRating, 5 stars2 weeks ago
"I loved my stay! The place was cozy and well-kept, with everything I needed. My host was super helpful and provided great recommendations for local attractions and activities. I felt right at home. Highly recommend!"

Quick stats about house rentals in Chester

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    410 reviews

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Kroger, Lowe's Home Improvement, and Sonic Drive-In

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